(+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids

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Title: (+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids
Author: Sandelier, Matthew J.
Advisors: Daniel L. Comins, Chair
Suzanne Purrington, Member
Samuel Levine, Member
Abstract: This work develops a general synthesis of the Prosopis africana alkaloids, using a chiral auxiliary-mediated process. Enantiopure N-acyldihydropyridones were produced and used as intermediates, targeting (+)-desoxoprosopinine as a synthetic model for those alkaloids. The orientation of all three stereocenters was highly controlled, with the synthesis of intermediate 75, just short of the target, in 7steps with a 13.8% overall yield.
Date: 1999-06-04
Degree: MS
Discipline: Chemistry
URI: http://www.lib.ncsu.edu/resolver/1840.16/1654


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